In this heartfelt episode of Holiday AF, singer and songwriter MAJOR. joins co-host and best friend Deborah Joy Winans Williams to reflect on growing up in a massive blended family in Houston, where Christmas meant joy, noise, food, and togetherness. MAJOR. shares how his family created the December 26th tradition, a day reserved exclusively for siblings and their children, and how their Secret Santa ritual became a celebration of generosity and laughter. He also opens up about his blossoming relationship with someone he’s known since high school and how love has brought new meaning to both his music and the holiday season. The two reminisce about humble beginnings, dreaming over Denny’s nachos, and the faith it took to get from there to now. The episode culminates in a stunning series of live Christmas performances from MAJOR., showcasing his signature tone, spirit, and musicality. Filled with humor, vulnerability, and vocal brilliance, this episode celebrates love, family, and holiday joy.

In this heartfelt and humorous episode of Holiday AF, Jemele Hill and Ian Wallace join hosts Deborah Joy Winans Williams and MAJOR. for a conversation rooted in Detroit culture, family legacy, and joyful holiday chaos. Jemele shares how her grandmother shaped her love for Christmas, what it meant to grow up with a December 21st birthday, and how moving to Los Angeles changed — and didn’t change — her seasonal traditions. The discussion shifts into Jemele’s evolution as a journalist and cultural commentator, detailing her transition from ESPN to The Atlantic and her acclaimed podcast Jemele Hill Is Unbothered. She talks about journalism as freedom work, why storytelling matters, and how she chooses compelling voices for her platform. The episode closes with a spirited round of “What Bothers You More?”, unpacking Christmas décor debates, partner preferences in spades and charades, and a playful moment choosing between media icons Carrie Champion and Michael Smith. It’s a festive blend of laughter, love, legacy, and cultural truth.

In this lively and culturally rich episode of Holiday AF, photographer and filmmaker Elton Anderson sits down with hosts Deborah Joy Winans Williams and MAJOR. to share stories from Detroit, Liberia, and his travels across the globe. Elton discusses how he fell in love with photography at 27 and how his platform Creators of Color was born from a desire to increase representation behind the camera. He also gives an inside look at his travel show Lens of Culture, which has taken him everywhere from Puerto Rico to Ghana to the Dominican Republic. Elton reflects on the holiday traditions that shaped him growing up — from massive Detroit family gatherings to navigating holidays as a constantly traveling creative. He reveals why Zanzibar feels like his dream Christmas destination and how travel continues to deepen his connection to culture and community. The conversation takes a hilarious turn during the Naughty or Nice game, where Elton shares confessions about past relationships, holiday gift mishaps, and globe-trotting romantic adventures. This episode captures the humor, warmth, and cultural depth that make the holidays meaningful through Elton’s unique lens.

In this heartfelt episode of Holiday AF, actress and activist Logan Browning sits down with hosts Deborah Joy Winans Williams and MAJOR. to reflect on the traditions, values, and joy that shaped her holiday memories. Logan revisits her childhood home — a lively, generous space where relatives, friends, and neighbors gathered, slept wherever they could, and always received a gift regardless of how unexpected their arrival was. She also shares how her family’s traditions have evolved, from full-house celebrations to playful white elephant exchanges and budget-friendly gift rituals. The conversation touches on Logan’s artistic upbringing, her connection to activism, and how storytelling first shaped her understanding of justice and community. Things take a fun turn as Logan plays Holiday AF’s rapid-fire game, offering hilarious and heartfelt opinions on everything from fake vs. real Christmas trees to holiday desserts, board games, and tropical vs. snowy celebrations. Her wit, warmth, and competitive spirit make this episode a festive delight.

In this festive episode of Holiday AF, multi-talented entertainer Trevor Jackson joins hosts Deborah Joy Winans Williams and MAJOR. to revisit the holiday memories that shaped his upbringing. Trevor dives into stories from snowy Indiana winters, including braving blizzards and icy walks that turned into family legends. He also shares the warmth of holiday gatherings at his grandmother’s home and why returning to family feels like recharging his spirit. The conversation is filled with laughter as Trevor takes on the Holiday AF “Finish the Lyric” challenge, singing through iconic Christmas songs with charm and humor. From holiday traditions to dream destinations like Hawaii, Trevor brings both sincerity and levity to the couch. The episode concludes with a playful chocolate-tasting moment and a heartfelt holiday sendoff. This episode brings together nostalgia, music, culture, and seasonal joy — a perfect listen for fans of Trevor Jackson and holiday storytelling.

In this warm and entertaining episode of Holiday AF, actor Ser’Darius Blain joins hosts Deborah Joy Winans Williamsand MAJOR. to explore the rich holiday traditions shaped by his Haitian, Dominican, and Southern roots. Ser’Darius recounts the foods, rituals, and last-minute holiday planning that defined his Miami upbringing — from cornbread and collard greens to griot, curry goat, and family phone chains that came together into joyful, improvised celebrations. He also opens up about discovering acting while on a pre-med track, dropping out of medical school to pursue his passion, and moving to New York, where he experienced his first snowy Christmas. Ser’Darius shares behind-the-scenes stories from Jumanji, his journey to landing the role, and the surreal experience of watching major stars work up close. As an adult, he’s created a new holiday tradition of flying his family to different destinations — from New York to Big Bear — believing the gift of exposure is one of the greatest gifts he can offer. The conversation closes with fun insights into his culinary talents and his holiday meal-prep company, King’s Cuisine. This episode blends multicultural heritage, comedy, and holiday warmth into an uplifting seasonal listen.

In this heartfelt and humorous episode of Holiday AF, actor Will Catlett reflects on the traditions and values that shaped his winter holidays growing up in Del Ray, Virginia. Will shares stories of cold-weather Christmases, his mother’s beautifully decorated tree, and the Black snowman that proudly sat in their window — a symbol of cultural joy and representation. Now experiencing his first Christmas as a father, Will discusses how parenthood deepens his artistry and expands his understanding of love, legacy, and what it means to raise a child during the holiday season. He opens up about discovering acting unexpectedly in college and how one moment of curiosity led him to a destiny-shifting acting class. With warmth and humor, Will joins the hosts for the Holiday AF acting challenge, improvising as an exhausted elf named Heathcliff and stepping into a comedic Santa Claus skit. The episode closes with Will’s reflections on artistry as a form of service — a way to affect change in the hearts of humanity. A rich blend of comedy, heart, culture, and holiday spirit, this episode highlights Will Catlett’s depth, talent, and generosity.

In this heartfelt and festive episode of Holiday AF, actress and writer Michele Weaver opens up about her creative beginnings, her unexpected path into the entertainment industry, and the holiday traditions that shaped her life. Michele shares stories of growing up in snowy Denver, where Christmas never felt complete without white powder on the ground — even praying as a child for snowfall as a sign that “everything was going to be okay.” She also dives into her early career hustle, from modeling for a makeup company to answering phones and training as an airbrush artist while pursuing acting without an agent. Michele reflects on directing The Glass Menagerie in high school, collaborating with Deborah on a short film, and now stepping into her starring role in a new NBC family drama. The conversation brings plenty of laughs as Michele discusses her lifelong love for eggnog (even dairy-free versions), her family’s name-draw gift tradition, and the rules everyone tries to follow when sticking to a holiday budget. A warm, insightful, and joyful episode that celebrates creativity, friendship, and the magic of holiday memories.

In this uproariously funny episode of Holiday AF, comedian KevOnStage joins hosts Deborah Joy Winans Williamsand MAJOR. to break down the real, raw, and ridiculous sides of Christmas. Kev shares memories from broke childhood holidays — including missing gifts, wrong-sized sweaters, and the legendary Batman car that arrived without Batman. Despite it all, the joy, food, and family time made those holidays unforgettable. Kev also explains why he now chooses experiences over gifts, taking his kids on international Christmas trips to help them build a true sense of cultural awareness and global love. From Amsterdam bike culture to upcoming adventures in Japan, Kev reveals why memories beat material items every time. As a comedian who happens to be a Christian, Kev talks about navigating faith with honesty and humor, recalling moments from church that shaped his comedy. The episode wraps with a playful holiday rapid-fire game covering Christmas drinks, NBA traditions, and the ultimate debate: who in the family spikes the eggnog? A warm, hilarious, and refreshingly honest take on holiday joy.

In this festive and joy-filled episode of Holiday AF, hosts Deborah Joy Winans Williams and MAJOR. sit down with actress and comedian Bresha Webb to explore the traditions, humor, and heartfelt moments that make the holidays special. Bresha reflects on growing up in the Webb household, where her father’s Christmas breakfast and her mother’s homemade apples created cherished yearly rituals. As her parents age, she shares how her role in maintaining family traditions has shifted — from flying them to Los Angeles to hiring a chef when her mother “retires” from cooking. Bresha also talks about her dramatic turn in Tyler Perry’s A Fall From Grace, discussing what it meant to step into a new kind of character and work alongside icons such as Cicely Tyson and Phylicia Rashad. The conversation blends depth with pure comedy as Bresha brings unforgettable impressions — from DMX to Britney Spears — transforming holiday classics into comedic gold. This episode captures the warmth, joy, and laughter of the holiday season while showcasing Bresha’s talent, heart, and festive spirit.

In this lively and heartfelt episode of Holiday AF, actor Tye White joins hosts Deborah Joy Winans Williams and MAJOR. to share what Christmas looks like now that he’s married — from celebrating in Los Angeles to adjusting to his wife’s London-based family traditions. Tye breaks down the cultural differences between American and British Christmases, from missing mac and cheese and collard greens to discovering Yorkshire pudding and roast dinners. He also reflects on his early acting days with Deborah on Greenleaf, their instant on-screen chemistry, and the joy of stepping back into character for a Holiday AF version of the “Newlywed Game.” A die-hard Christmas lover, Tye admits his holiday season starts right after Halloween, complete with Temptations Christmas on loop and heavily spiked drinks throughout the day. This episode blends humor, culture, nostalgia, and the joy of evolving family traditions — capturing both the chaos and the warmth of the holiday season.